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Electron injection for aromatic metamorphosis of indole
Author(s) -
Yorimitsu Hideki
Publication year - 2021
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.202000369
Subject(s) - chemistry , heteroatom , aromaticity , pinacol , metamorphosis , indole test , ring (chemistry) , combinatorial chemistry , molecule , organic chemistry , catalysis , botany , larva , biology
Aromatic metamorphosis, endocyclic transformations of aromatic compounds, has been emerging as a new synthetic strategy in organic synthesis. This counterintuitive strategy necessitates very powerful reactions that can surmount aromaticity and the strong carbon–heteroatom bonds of the heteroaromatic rings. This Short Account describes the development of the currently most powerful elementary reaction for aromatic metamorphosis, which is electron injection from lithium metal. Exceptionally robust and aromatic N ‐phenylindole is subjected to the electron injection, resulting in the formation of the corresponding dianionic intermediate through reductive ring‐opening. A trapping reaction of the dianionic intermediate with organoboronic acid pinacol esters provides benzazaborines, which are attractive BN‐isosteres of naphthalenes. The electron injection helps establishing aromatic metamorphosis as a reliable synthetic methodology to provide novel useful molecules.